Hello elcpu,
From what I understand the iTunes storage bar will show an estimation of what the storage will be on the device after each sync. Not necessarily what is currently on the device.
For example, If you select to sync a movie or other content to your device the storage bar at the bottom of iTunes will show an increased usage even though you have not actually transferred that content over to the iPhone/iPad.
iTunes should be checking the iPhone/iPad to see how much data "Documents & Data" and "Other" is being used but it is often a rounded number and not as accurate or as broken down as when displayed on the iPhone/iPad. Any content that cannot be syncing through iTunes can be displayed in the iTunes storage bar as Other, Documents & Data, or not even listed.
I hope this information is correct as it's what I was told by AppleCare support when working on a issue with "Other" taking up several GBs. From little tests that I have done with my own library it seems to be fairly accurate although difficult to keep track of. I hope this helps out.